


What did you do with the Cartwright Twins?

by waywardangel (leviarty)



Category: Supernatural
Genre: Anal Fingering, Anal Plug, Anal Sex, Bottom Castiel (Supernatural), Bottom Dean Winchester, Cartwrights do no engage in sexual acts with each other just with Dean, Comfortably Bisexual Dean Winchester, Creampie, Dirty Talk, Established Relationship, Face-Sitting, Gentle Sex, Gentleness, M/M, Multi, Multiple Orgasms, Orgasm Delay, Post-Episode: s13e16 Scoobynatural, Rimming, Rough Sex, Shameless Dean Winchester, Switching, Threesome - F/M/M, Top Castiel (Supernatural), Top Dean Winchester, threesome is in the past but it's pretty explicitly described
Language: English
Status: Completed
Published: 2021-01-11
Updated: 2021-01-11
Packaged: 2021-03-15 01:22:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,928
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28680312
Author URL: https://archiveofourown.org/users/leviarty/pseuds/waywardangel
Summary: Dean promised to tell him all about it later.
Relationships: Castiel/Dean Winchester, Dean Winchester/Cartwright Twins
Kudos: 57





	What did you do with the Cartwright Twins?

**Author's Note:**

> So this was originally started as a future scene in [Break the Cycle](https://archiveofourown.org/works/26091682) but even before I finished writing it, I knew it didn't quite belong there. Part of it may still end up there, but this version is far too kinky for the story that is trying to tell. Anyway. Enjoy!

When they got back from the case—an actual, honest-to-god Scooby-Doo case with a Winchester twist—Dean paid up on his promise to Cas.

“So, the Cartwrights,” he started. “I don’t usually go for threesomes with people who are related, but—”

“Dude! Can you at least wait until I’m out of the car?” Sam said.

Dean grinned and shot Cas a wink, as his brother rushed into the bunker. “They were so hot, man. And they were into it, but not into each other. That definitely made it less weird. Chloe and Ethan I think? Something like that. Anyway, they didn’t want to have sex with each other, just with me, and I mean, come on, who wouldn’t…” Dean paused for a moment, looking over at the angel as they walked toward the bunker (at a slow enough pace that they wouldn’t catch up with Sammy). “Should I be telling you this?”

“I’m not jealous of any of the numerous people you’ve slept with over the years, if that’s what you mean,” Cas said. “Please, continue.”

Dean frowned. “I’m choosing to ignore the implication that you think I was a slut, but only because it’s true,” he said. They reached the kitchen, and Dean grabbed a couple beers from the fridge, popped them both open, and passed one to Cas. “Anyway. They had definitely done this before—a threesome, I mean. I hadn’t, for the record. Always kinda thought it would be too much to focus on.”

“But you enjoyed it?”

“Oh, hell yeah. She had, like, no gag reflex, which is great, but he did this thing with his tongue… you know, it seems to gross to even say it out loud, but I swear, it felt amazing.”

“Perhaps you could show me?”

Dean grinned, and tugged at the angels beltloops, pulling him closer. “Yeah, I could do that,” he said, planting several quick kisses on his lips. “Could you imagine the look on Sammy’s face if he found out we did it in here?”

“People do eat in here,” Cas said. “We shouldn’t defile it.”

Dean took Cas’ beer from his hand, setting it down on the counter with his own. “The wrongness of it is what makes it fun,” he whispered in Cas’ ear, unbuckling his belt and then sliding a hand down, stroking Cas’ length through the thin fabric of his boxers.

“Dean,” Cas said, attempting to convey a warning, but it mostly came out as a moan.

“I’m just teasing, buddy,” Dean said, biting and sucking at his neck. “No kitchen-fucking while Sammy’s in the house.” Maybe he could convince him some other time though, when they were really alone. “Come on.” He sucked just a little harder at Cas’ neck as he fixed up his pants, then pulled him down the hall.

“So, the girl, Chloe or whatever, she’s deepthroating me like she does it every day, like she doesn’t even need to breath, and her brother is behind me, getting me ready so he can fuck me good and proper. It was so much, I’m surprised I made it to the main event.” Just thinking about it was getting him hard again. (Though, perhaps it was also thinking about what he was about to do to Cas.) “Probably the worst part of a threesome is the logistics, ya know? Making sure everyone’s got something to do and no one’s feeling left out. So he’s still opening me up, but if she keeps blowing me like this, I’m done for. So we move around, get into a position where she can sit on my face…”

He pushed his door open and stopped briefly to look at Cas, and was right to do so. He laughed at the predictably confused look on the angel’s face.

“That doesn’t sound pleasant.”

“Nah, man, it’s not like that. I mean, sure, there are people who don’t like it, but I love it. It’s… well, she’s naked, right, so when she ‘sits’ on your face, she’s not fulling sitting, just putting her honeypot where your mouth is.” Cas still wore the same perplexed expression, though was now distracted by Dean’s hands as they went to work unclothing them both. “Her vagina, I’m taking about her vagina.”

“No, I understand. There are unnecessarily many nicknames for human genitalia, but I understand. The purpose is to bring her pleasure. Go on.”

Dean snorted. “So, I’m eating her out, and he’s eating me out—babe, take your shoes off.”

Cas, suddenly remembering what they were doing, does as instructed, removing his shoes so Dean could continue removing his clothing.

“You’re enjoying this?” Dean asked as his hands found their way to Cas’ rapidly hardening cock. “You like hearing me talk about all the dirty things they did to me?”

Cas hummed. “It would appear so, yes. Please, go on.”

Dean chuckled. “It’s gonna be a lot harder to tell the story once I’ve got my mouth on you. You trust me?” Dean asked, nibbling at Cas’ earlobe.

“Of course.”

“Turn around,” he said, dropping to his knees as Cas did. Dean spread his cheeks then ran his tongue between them.

“ _Oh_ ,” Cas breathed.

Dean grinned as he got to work opening him up, first with his tongue, then bringing his fingers into the mix as well.

“Dean, this is—” Cas braced himself against the wall, letting out a long moan.

“I know, I know,” Dean said, pulling his tongue out, then his fingers. Cas whimpered at their absence. Dean rose to his feet again, kissing Cas’ back and neck. “Lie down on the bed, okay?”

Cas nodded, seemingly incapable of forming words. One peek over his shoulder and Dean could see exactly why—the angel was achingly hard, dripping pre-come onto the carpet.

Cas moved to the bed, as Dean crossed the room to find something in his dresser.

“I feel silly,” Cas said, finally finding his voice.

Dean glanced over at him. Cas was lying on his back, his dick still standing at attention. “You look fucking hot,” he said. He brought out a bottle of lube, and a plug. He popped the cap, then coated his fingers and the plug before moving back toward the bed. His now-slick fingers slide easily into Cas, making sure he was well-lubed. Cas moaned, his eyes closing as his head rolled back to the pillow. But Dean removed his fingers again all-too quickly.

“ _Dean_ ,” he groaned.

Dean shushed him gently. He lined up the plug and eased it inside. It wasn’t as big as his cock would’ve been, but it was just the right size and shape that Dean knew it would hit all the right spots. As it slid into place, Cas let out another moan, wiggling around as he chased the feeling it brought.

Dean squeezed more lube onto his fingers, but this time reached behind himself, slipping one finger, and then another, inside to work himself open.

“Perhaps you could continue your story.”

Dean smirked. “Yeah, okay,” he said, pausing his ruminations to press a kiss to Cas’ lips. “But only if you promise not to touch yourself.”

Cas whined. “That hardly seems fair.”

“I don’t want you to come yet. Not until I say. Okay?”

Cas nodded.

“Okay,” Dean said softly. He continued to work himself open, trying to remember where he had left off. “So. He’s eating me out, right, and it’s the best fucking thing. I’m surprised I made it through that. And she’s above me, moaning and crying through her first orgasm, but they just keep going.”

Dean watched as Cas bites his lip, willing himself not to touch. His eyes flutter closed.

“No, no,” Dean whispered. “Watch me?”

Cas’ eyes opened again, piercing blue as they stared at Dean.

“And I’m so fucking ready to get railed by this guy, you know?”

“I think I am familiar with the sensation,” Cas said, his voice dripping with sarcasm and frustration.

Dean grinned. “I know, buddy. Almost there, I promise. I think he knew I was getting impatient, too. So he gets up, and she climbs off my face, and the next thing I know, his dick is sliding home, and it feels so, so damn good. But it’s even better than that, because she’s climbing back on top.” Dean takes that moment to climb on top of Cas, positioning himself just over his throbbing cock. “She slides down onto me,” he said, moaning as he did the same to Cas.

“ _Dean_.” Cas’ own moan was louder and longer. 

“I know, baby, it feels so good.” Dean rose off him, the ground back down. “She was so wet and warm and tight, and he was thrusting into me like there was no tomorrow. She was riding me, and he was fucking me, and I could barely fucking _think_ , let alone move. I was just along for the ride.” He had a little more control here; it was Cas who was too far gone to do anything more than moan and whimper as Dean rolled his hips and rode him through. “I came like a fucking freight train,” he said, grinding down. “Probably one of the best orgasms of my life. That was before I met you, of course.”

He wasn’t saying it just to say it, either. The orgasms he had with Cas were easily the most intense he’d ever experienced.

He leaned forward, bringing his lips to Cas’ ear. “You can come now,” he said. “Whenever you’re ready.”

Cas whimpered again as Dean picked up the pace, until finally Cas came, filling him up.

“ _Fuck_ ,” Dean moaned as he could still feel Cas coming a while later, filling him fuller than ever before. Dean kept riding him through it, milking him for every drop he had and then some.

“You haven’t climaxed yet,” Cas said, when his head had cleared. Dean had gone still, his eyes closed with his head tilted toward the ceiling. Cas was still inside him, holding all his spunk in place, though Dean could feel him going soft.

Dean hummed. “Kinda thinking about coming inside you,” he said thoughtfully. “If that sounds agreeable to you, anyway.”

“Oh? Any preference as to where?”

“Not really.”

“Then how about,” Cas said, rolling them over and pinning Dean to the mattress. “We put this pretty little plug to good use, then you can fuck me until I come again?” Cas reached behind himself, pulling the plug free. A moment later, he was slipping out Dean, and Dean could feel his spunk start to dribble out a little before the plug was slipping in, closing him up again.

“Not sure I’m gonna make it that far, babe,” Dean said. He was already so close, and angelic refractory period or no, Cas was only what could generously be considered half-hard again.

“Why don’t you try for me?” he asked softly, pressing a kiss to Dean’s lips.

Dean nodded blearily as Cas moved to reposition them again. The plug was pressed against his prostate, making it that much harder to hold on, especially as they moved.

Cas pulled his knees up, drawing Dean in close, then wrapped his legs around his back as Dean bottomed out, thrusting into him.

He held out as long as he could, but in the end, it wasn’t quite long enough. He came deep inside Cas, while the angel stroked himself, rubbing off that second orgasm a few moments later.

Dean collapsed on top of him, pinning the mess between them. He nuzzled Cas' neck. "Love you," he mumbled before drifting off.


End file.
